How to Draft Client Letters With Claude

Client letters tend to go one of two ways when they're rushed. Either they get buried in hedging and defined terms until the actual news is hard to find, or they get flattened into something so brief it reads as evasive. Both versions technically inform the client. Neither one reads like it was written by a person who has their case in mind. An associate firing off a two-line update between hearings and a partner burying the same update in three paragraphs of throat-clearing have both technically communicated the news, and both have left the client slightly worse off than a clear letter would have.

A client letter has exactly one job: make the reader understand what happened and what happens next, in that order.

Why the first draft usually needs a rewrite, not just a proofread

The instinct under time pressure is to start from whatever letter you sent last time and swap the details. That saves time on structure, but it also imports the previous letter's tone, even when this update calls for something different. A letter announcing a favorable ruling and a letter announcing an unfavorable one shouldn't sound like the same document with different nouns, but reusing a template without rethinking the tone is exactly how that happens.

Take an associate who drafted a calm, routine-sounding letter about a procedural extension last month, and reaches for the same template this month to announce a denied motion. The structure still fits, but the register is wrong: what worked for genuinely minor news reads as strangely muted when the news is actually a real setback. The client either misreads the severity of what happened, or notices the mismatch and starts to wonder whether the firm is downplaying something.

Generic: "Please be advised that opposing counsel has filed a motion for extension of time, which this office does not oppose."

Specific: "Opposing counsel asked for an extra 30 days to respond, and we don't object. That pushes the trial date to March, but doesn't change our strategy."

The second version tells the client what happened, what it means for them, and what doesn't need to worry them, in three short sentences instead of one long one.

What a clear client letter actually needs

Getting there fastest means giving Claude the situation directly, not a half-drafted letter to patch up:

For a client you haven't worked with long enough to know their typical reaction, it's worth asking Claude to draft a version that states the news plainly without assuming an emotional register either way, so you can add that calibration yourself once you know more about how they tend to respond.

Matching the letter to the actual news

The same process that produces a calm letter for routine news needs a different pass when the update is genuinely bad. Softening real bad news until it reads as neutral isn't kindness, it's a disservice, and clients tend to notice the gap later when the full impact lands. A client who reads a denied motion described in the same even tone as a routine scheduling update may not grasp how much the case's posture just changed, and that gap in understanding tends to surface later as a harder conversation than the one you could have had upfront.

Iterating without starting over

The first draft rarely lands exactly right, and that's fine. The efficient move is refining through conversation rather than rewriting from scratch each time.

Iteration works the other direction too: a draft that's accurate but reads as cold for a longtime client who expects a more personal register is worth naming explicitly, rather than assuming the only failure mode is being too formal.

Continue reading

• Reviewing Contracts with Claude Without Missing the Risky Clause: the review this kind of letter often reports back on.
• Turning Deposition Notes into a Clear Case Summary: for when the update you're writing about comes from witness testimony rather than a filing.